p-Toluenesulfonic acid → N'-{2,5-dimethyl-4-[2-(methyl-phenyl-amino)-pyrimidin-4-yloxy]-phenyl}-N-ethyl-N-methyl-formamidine

HRID 12081

Reaction equation

HRID 12081 reaction equation
[NH2:1][C:2]1[C:22]([CH3:23])=[CH:21][C:5]([O:6][C:7]2[CH:12]=[CH:11][N:10]=[C:9]([N:13]([CH3:20])[C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[N:8]=2)=[C:4]([CH3:24])[CH:3]=1.COC(OC)OC.[C:32]1([CH3:42])C=CC(S(O)(=O)=O)=CC=1.[CH3:43][NH:44][CH2:45]C>>[CH3:23][C:22]1[CH:21]=[C:5]([O:6][C:7]2[CH:12]=[CH:11][N:10]=[C:9]([N:13]([CH3:20])[C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[N:8]=2)[C:4]([CH3:24])=[CH:3][C:2]=1[N:1]=[CH:43][N:44]([CH2:32][CH3:42])[CH3:45]

Participants

5

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 9005Trimethyl orthoformateHCID 12219N-MethylethylamineHCID 67026468[4-(4-Amino-2,5-dimethyl-phenoxy)-pyrimidin-2-yl]-methyl-phenyl-amine

Product 1

HCID 16004709N'-{2,5-dimethyl-4-[2-(methyl-phenyl-amino)-pyrimidin-4-yloxy]-phenyl}-N-ethyl-N-methyl-formamidine

Procedure

To a mixture of 252 mg (0.7 mmol) of [4-(4-Amino-2,5-dimethyl-phenoxy)-pyrimidin-2-yl]-methyl-phenyl-amine and 4 ml of trimethoxymethane, 20 mg of p-toluene sulfonic acid were added. The reaction mixture was refluxed for 2 hrs and concentrated in vacuo. The mixture was solved in 10 ml of dichloromethane and 62 mg (1.05 mmol) methyl ethyl amine was added. After stirring 18 hrs at ambient temperature the mixture was evaporated and yielded 280 mg (89%) with a purity of 87%; log P (pH 2.3)=1.61.

Workup

  1. additionwere added
  2. temperatureThe reaction mixture was refluxed for 2 hrs
  3. concentrationconcentrated in vacuo
  4. customwas evaporated
  5. customyielded 280 mg (89%) with a purity of 87%

Sources & evidence

ORD record
ord-5891a95dbe0a4f5487ba99d0197a9015
Source dataset
uspto-grants-2010_06
Patent number
US07727986B2

Linked notes

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